Ms. AN I 8 in the University Library of Basel contains the second part of the Commentary on the so-called “unread” orations of Saint Gregory of Nazianzus composed by Elias the metropolitan of Crete presumably around 1120, a text that was rarely copied in Byzantium. This essay examines the hitherto little-studied miniatures that were added to the codex, two author portraits and fourteen illustrative frontispieces. Stylistic and especially iconographic evidence suggests that the book’s miniatures were commissioned during the reign of Emperor Manuel I Comnenus (1143–1180), most likely in or after 1166 when Manuel assembled a Church Council in the Great Palace of Constantinople which dealt with the interpretation of Christ’s phrase “My Father is greater than I” (John 14:28). The essay presents the first detailed analysis of the iconography of the miniatures in light of the theological writings contained in the volume. Painted at a time of intense doctrinal debates, I argue that these images first and foremost serve to celebrate Gregory as a religious leader and teacher of lasting authority in matters of Byzantine Orthodox theology. Codicological analysis reveals a complex production scenario and suggests that at least the frontispieces were added to the book as an afterthought; furthermore, it can be demonstrated that these paintings were not originally intended for the present volume but likely for another copy of the same text. Yet it seems that all sixteen miniatures were created within a short period of time by one and the same workshop comprising a large number of painters, who collaborated on what appears to have been a commission of highly unusual character.